Clearwater, FL Vacation Rentals

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303 beach rentals

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Luxurious Beachfront Condo at Redington Towers

Redington Shores condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Shared outdoor pool (unheated) Swing set or jungle gym

All filters match

Price per night from

$344

ROYAL REXHOST RESORTS – Madeira Beach Yacht Club (MBYCC)

Madeira Beach guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Shared outdoor pool (unheated) Swing set or jungle gym

All filters match

Price per night from

$172

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BAYFRONT CONDO ON TAMPA AY

Tampa condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 2 hours 7 minutes

1 of 2 match: Shared outdoor pool (unheated), Swing set or jungle gym

1 of 2 filters match

Price per night from

$216

Beachy Clearwater is Great! Pets Welcome

Clearwater house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

1 of 2 match: Swing set or jungle gym, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$92

Clearwater Beach Condo 2 B|R fits 5-8 ppl

Clearwater apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 28 minutes

1 of 2 match: Swing set or jungle gym, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$172

Lovely Tropical Sunlit bedroom

Clearwater house

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Swing set or jungle gym, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$228

Florida Home with Private Fishing Pond- See Nature Not Neighbors

Odessa house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Shared outdoor pool (unheated), Swing set or jungle gym

1 of 2 filters match

Price per night from

$143

Best Vacation Spot

Clearwater b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Shared outdoor pool (unheated), Swing set or jungle gym

1 of 2 filters match

Price per night from

$86

Tropical Tiny spa home

Tarpon Springs cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Responds fast! avg. 1 hour 18 minutes

1 of 2 match: Shared outdoor pool (unheated), Swing set or jungle gym

1 of 2 filters match

Price per night from

$114

Nash Street Oásis

Clearwater house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 12

1 of 2 match: Shared outdoor pool (unheated), Swing set or jungle gym

1 of 2 filters match

Price per night from

$286

Pink Gulfside Cottage, 100 steps to beach, Pet OK, Restored Beach House

Clearwater house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Shared outdoor pool (unheated), Swing set or jungle gym

1 of 2 filters match

Price per night from

$285

BoHo Style Home [Playset, Patio / 5 min Clearwater Beach]

Clearwater house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

1 of 2 match: Shared outdoor pool (unheated), Swing set or jungle gym

1 of 2 filters match

Price per night from

$206

Clearwater Sugar Beach

Clearwater apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 1

1 of 2 match: Swing set or jungle gym, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$85

Casa Daniella

Clearwater house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 2

1 of 2 match: Swing set or jungle gym, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$201

Beautiful Boho Style Condo

Clearwater condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Swing set or jungle gym, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$217

1 of 2 match: Swing set or jungle gym, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$326

Clearwater Vacation Beach 2 B/R Condo fits 6ppl

Clearwater condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 28 minutes

1 of 2 match: Swing set or jungle gym, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$149

Amazing Condo and Breathtaking Views!

Indian Rocks Beach condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

Responds fast! avg. 3 hours 36 minutes

1 of 2 match: Swing set or jungle gym, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$600

Steps from Beach, Pets OK, Sleeps 6, Clearwater Beach. 2 Bedrooms

Clearwater apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Shared outdoor pool (unheated), Swing set or jungle gym

1 of 2 filters match

Price per night from

$377

1 of 2 match: Shared outdoor pool (unheated), Swing set or jungle gym

1 of 2 filters match

Price per night from

$422

Palm Harbor Waterfront, Game room, Kayaks and more

Palm Harbor house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 12

1 of 2 match: Shared outdoor pool (unheated), Swing set or jungle gym

1 of 2 filters match

Price per night from

$457

Lemon Cottage, Pets OK , 200 Steps to Beach

Clearwater cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared outdoor pool (unheated), Swing set or jungle gym

1 of 2 filters match

Price per night from

$296

“Great cozy home away from home.” We stayed in the Orleans bungalo apartment on July 15-18. It felt like we were at home. The apartment had lots of character and charm. Loved sitting outside on the terrace watching the free entertainment across the street , was it called the ship wrecked bar? I especially loved beiing able to go to the back alley and washing clothes. (I hope it belonged to the cottages property, if not then oops!) We utilized the kitchen and the gas grill out back on the patio.Everything was great and this cottage had plenty of space for two families. We met my cousins from Texas in Flordia for a vaca. We drove from Oklahoma. The flat screens worked great. I have no complaints about this place. I just want to say to all you all snotty people leaving negative comments.... Quit complaining or find somewhere else to stay. What exactly do you think you are getting when you hear the word "cottages" it's not going to have a bell hop and a maid that cleans up your messes daily. Maybe some of you never lived in 100 year old homes and only used to a lavish lifestyle. Obviously you spent your time in doors. not us we were at the beach the majority of the day until almost 9pm every night. I enjoyed my stay there. It was a good 3 day stay for us despite the rainy weather. Yet we still had fun.

1 of 2 match: Shared outdoor pool (unheated), Swing set or jungle gym

1 of 2 filters match

Price per night from

$297

Aqualea at Hyatt Regency, Clearwater Beach FL

Clearwater apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 5

1 of 2 match: Swing set or jungle gym, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$344

Clearwater Beach Resort Apartment with Oceanview

Clearwater apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

Responds fast! avg. 3 hours 54 minutes

1 of 2 match: Swing set or jungle gym, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$424

Condo Penthouse with Pool And Hot Tub

Tampa condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$237

Regatta Beach Club 414S '90 day min stay with 2 week lead time'

Clearwater condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 50 minutes

1 of 2 match: Swing set or jungle gym, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$103

Chateau 5W Beachfront on the Beautiful Belleair Beach

Belleair Beach apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 50 minutes

1 of 2 match: Swing set or jungle gym, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$153

Luxury waterfront Condo Rooftop Terrace

Clearwater house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$567

Bayside Condos 17 Waterfront Studio

Clearwater apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Responds fast! avg. 50 minutes

1 of 2 match: Swing set or jungle gym, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$99

Madeira Towers 302 Beachfront 3 bedroom 2 bath at Madeira Towers

Madeira Beach condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 50 minutes

1 of 2 match: Swing set or jungle gym, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$387

Gulf Belleair Beach Condo 325 Condo located on Belleair Beach

Belleair Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 50 minutes

1 of 2 match: Swing set or jungle gym, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$133

Brightwater Point Condo 106 Amazing Water View Condo

Clearwater apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 50 minutes

1 of 2 match: Swing set or jungle gym, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$561

Landmark Tower 1707 Charming 17th Floor Oceanfront Condo

Clearwater apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 50 minutes

1 of 2 match: Swing set or jungle gym, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$137

Bay Harbor 501 Beautiful 5th Floor Waterfront Condo

Clearwater apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 50 minutes

1 of 2 match: Swing set or jungle gym, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$885

Barefoot Beach Resort F110 Waterfront pool and short walk to the beach

Indian Shores condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 50 minutes

1 of 2 match: Swing set or jungle gym, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$876

ROYAL REXHOST RESORTS – Madeira Beach Yacht Club (MBYCC)

Madeira Beach house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Swing set or jungle gym, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$161

ROYAL REXHOST RESORTS – Madeira Beach Yacht Club (MBYCC)

Madeira Beach house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Swing set or jungle gym, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$172

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